: While the DeCastro Sisters had the first hit, Dinah Washington's 1954 soulful rendition is considered the definitive version and was inducted into the Grammy Hall of Fame. Other iconic covers include those by Frank Sinatra and Amy Winehouse . The TV Moment: Gilmore Girls

The title "Teach Me Tonight" is also the name of a pivotal Season 2 episode of Gilmore Girls , where the song's themes of "lessons" take a darker, more literal turn.

Written in 1953 by and Gene De Paul , the song uses a schoolroom metaphor to describe romantic initiation. It frames the act of falling in love as an education, with the "teacher" standing close enough for "graduation" to be imminent.

"Teach Me Tonight" is a classic jazz standard about the vulnerability and thrill of new love, but its "deep story" is best found in its clever metaphors and the high-stakes drama it inspired in pop culture. The Song: A Lesson in Love